Yarn conditioning process



.such materials amenable ations such as knitting, weaving, carding, spinin question that Patented Nov. 13, 1945 YARN CONDITIONING mooass John It. Caldwell, Kingsport, Tenn.', assignor to Eastman Kodak Company, Rochester, N. Y., a

corporation of New Jersey No Drawing. Application February 22, 1944,

Serial No. 523,477

scams. 117-1395) This invention relates to the conditioning of textile yarns, and particularly to the conditioning of yarns, threads, filaments and fibers composed of or containing organic derivatives of cellulose such as cellulose acetate, cellulose" propionate, cellulose butyrate, cellulose acetate propionate and cellulose acetate butyrate, to render to various textile .oper-' ning', twisting and the like.

As is well known in the textile industry, the manufacture, processing and use of yarns composed of or-containing organic derivatives of cellulose and similar synthetic materials give rise to numerous problems generally absent from the handling of natural yarns such as silk, wool, cottonand the like. One of the chief problems encountered in dealing with these synthetic materials is to so lubricate or soften and, in some instances, to both lubricate and soften, the yarn it will have the correct frictional characteristics, or drag, and the required flexibility for the specific purpose in view. In the handling of continuous filament yarn, for example, it is necessary to condition the material to reduce the tendency towardbreakage-of individual filaments when the yarn is subjected to mechanical strains such as are involved in passage of the yarn over rolls, guides, and other parts of the yarn-producing mechanism and in twisting, winding, reeling and similar operations. In the case of yarns intended for use on commercial knitting machinery, it is particularly important that the yarn be soft and pliable in order that it may conform to the contour of the needles and give a closely knit fabric freefrom cuts, pinholes, stitch distortion, laddering, misplaits and other common defects. I e

Another problem of major proportions presented by these synthetic yarns is their extreme tendency to pick up charges of static electricity, especially in such operations as twisting,'winding, warping, picking, carding, combing, drafting, spinning, and the like. This tendency is particularly aggravated in the case of cut staple fibers, since in the commercial use of such material it is normally subjected to a number of extremely severe operations such as picking, carding and combing, all of which tend to so charge the individual fibers as to make proper'web formation diflicult or impossible or to give the ultimate yarn an undesirable unevenness.

In some types of yarn, all three of the abovementioned problems of lubrication, softening and anti-static treatment are present and in any case .stances,

erly coordinated to accomplish the desired result is often a matter'of extreme difficulty. This is due to the fact that in any given. yarn conditioningcomposition, whetherprimarily designed for use as a warp, fillingor knitting lubricant, or as an anti-static, the various components and their functions must be delicately balanced one against the other so as to give a practical and commercially satisfactory yarn treatment.

Textile yarn treating compositions are generally applied in one of two forms, that is, a clear oil or an aqueous or other emulsion thereof. If the composition is to be applied in the form of anoil, itis important that it should remain a clear, homogeneous liquid two or more phases on standing. In many init is necessary to employ blending or solubilizing agents in order to preclude the pos sibility of such separation. In the case of emulsions, on the other hand, it is often necessary to employ agents which function to cause the various components of the composition to be efifectively and permanently dispersed throughout the dispersing medium. In addition it is, in general, necessary in those cases where the yarn treating composition contains oilsor oily materials which are normally insoluble in water to add emulsifying agents for the purpose of enabling these components to be removed from the yarns or fabrics to which they are applied in the ordinary aqueous scour baths.

The present invention has as its principal object to provide an improved process for the conditioning of textile yarns, threads, filaments and fibers, particularly those composed of or containing organic derivatives of cellulose such as cellulose acetate, cellulose propionate, cellulose butyrate, cellulose acetate propionate and cellulose acetate butyrate, to render such materials amenable to various textile operations and processes, such as knitting, weaving, spinning, carding,

drawing and the like. A further object is to proand not separate into particularly those composedbf or containing organic derivatives of cellulose, such as cellulose acetate, cellulose propionate, cellulose butyrate,

cellulose acetate propionate and cellulose-acetate butyrate, with stable yarn treating compositions or conditioning agents which arereadily susceptible of removal from the yarn by means of ordinary aqueous scour baths, characterized by the fact that such compositions are composed of or contain high molecularweight nitriles derived from fatty acids containing8-20 carbon atoms.

I have foundthat the nitriles possess unique and exceptionally valuable properties, not only as yarn lubricants per se, but as constituents of various yarn treating compositions r lubricants. While I limit myself to no theory regarding the efllcacy of the nitriles as ingredients of yarn conditioning compositions,-itis my belief that their exceptional lubricating properties'may be attributed to the fact that they contain a long hydrocarbon chain. I The presence of the long hydrocarbon chain also imparts solubility of these compounds in various hydrocarbon oils commonly employed as ingredients of yarn lubricating compositions and makes possible their use in association with said oils. In addition, these compounds are characterized by the presence of a nitrile, or -CEN. group which imparts miscibility with polar compounds such assoaps, sulfonated oils,ffatty alcohol sulfates andother compounds employed as emulsifying or dispersing agents in the compounding of textile conditioning compositions. The polar nitrile group also has theadvantage that'it permits high film strength and adhesion in the lubricating film deposited on the yarn.

I ave v strated that the long chain nitriles possess a most unusual and unexpected abilit to lubricate yarns to which they are applied, particularly yarns composed of or containingorganic derivatives of cellulose such as cellulose acetate and similar cellulose organic acid esters .and like materials. Moreover, these compoundsare bi-functional in that they combine the properties of a lubricant and a blending agent in one individual compound, that is, they can function not only as lubricants per se, or in association with other luby extensive experimentation 'demonbricants, but they have the unusual property of blending or solubilizing in various hydrocarbon oils, many compounds such as; soaps, sulfonated oils and the like employed as dispersing or emulsifying agents in textile conditioning compositions which are normally insoluble in, or incompatible with, such oils. In addition, since they are chemically neutral, the long-chain nitriles exert no deleterious action upon the yamrflbers themselves, nor do they induce corrosion of the metal parts of the yarn producing or processing machinery with which they may come in contact.

I have found that 'both the liquid and solid long-chain nitriles are of value as yarn lubricants. Those'which are liquid at ordinary temperatures-may be applied as such to the yarn as lubricants, while those whichare solid at ordithey impart to textile yarns a very low coefllcient of friction between the yarn surface and the surface of steel or porcelainguides such as are commonly employed in the textile industry. When applied, either alone or in combination with other yarn conditioning agents, they impart a soft, smooth hand or feel to the yamand greatly reduce the harshness or scroop generally resulting from the use of ordinary textile lubricants such ,as mineral oil.

. The nitriles may be readily prepared byany of the well-known standard procedures for the preparation of this class of compounds described in the chemical literature. The best method for preparing the nitrilesis through pyrolysis of the acid in. the presence of ammonia as'described by Italston and Harwood, J. Am. Chem; Soc. 59, 986

(1937); U. S. Patent No. 2,061,314. The physical properties of the straight chain fatty acid nitriles are described by Ralston, Selby, and Pool, Ind. Eng. Chem. 33, 682 (1941). The high molecular weight. nitriles employed in the process of the invention may be prepared b treating the corresponding carboxylic acid amide with phosgene as outlined in British Patent No. 488,036. They may also be produced by treating the carboxylic amides with thionyl chloride, as described by Oldham, J. Chem. Soc. 1939, p.201. Polymerized fatty acidinitriles may be prepared according to the method described in British Patent No.

Among suitable long-chain nitriles which may be employed in accordance with my invention as yarn lubricants per vse oras ingredients of yarn lubricating and conditioning compositions .are those derived from straight-chain saturated acids,,unsaturated acids, naphthenic acids, dibasic acids and variousmixed acids such as those present in naturally-occurringfats and oils such as coconut oil, olive oil and tallow. Typical examples of specific compounds are as follows:

I Nitriles from saturated acids Lauroniti'lle Myristonitrile Palmitonitrile Margaronitrile Stearonitrile Ricinoleic acid nltrile Nitrile of 9-phenyl stearic acid 9-hydroxy nonanenitrile 2-phenyl acetonitrile 3-phenyl propionitrile 9,10-dichloro octadecanenitrile Nitriles .0! dibcsic acids Suberonitrlle Azeleonitrile Sebaconitrile 'cluded merely for purposes Mixed nitrlles Nitriles of coconut oil fatty acids Nitriles of olive oil fatty acids Nitriles of tallow fatty acids In these compounds the nitrile may contain other groups or substituents, as would be the case with ricinoleic acid nitrile and the nitrile of 9-phenyl stearic acid. Additional examples ofnitriles derived from saturated acids are caprylonitrile, pelargononitrile, capronitrile, undecanenitrile, tridecanenitrile, pentadecanenitrile, eicosanenitrile, 2-ethyl hexanenitrile, 2-butyl hexanenitrile, and 3-ethyl octanenitrile. Nitriles-derived from naphthenic acids containing 8-20 carbon atoms may also be employed as above described.

As indicated above, the long-chain nitriles may be used alone or in combination with other yarn conditioning agents. For trile maybe applied to yarn in various stages of processing by means 'of wick, roll, spray, etc.', to the extent of 0.3-10.0% based on the weight of the yarn. Nitriles which are solids or semisolids at room temperature may be dissolved in a volatile solvent such as toluene or a suitable petroleum fraction, and applied by-known means. Yarns lubricated in this way are characterized by extremely low friction when passed through porcelain or steel guides.

The nitriles have their widest application as a component of mixed oils or lubricants. Because of their molecular structure which embodies a relatively long hydrocarbon chain in combination with the polar nitrile group -C -N, they are valuable blending agents.- The hydrocarbon chain imparts the property of solubility in-oils, while the nitrile group tends to give miscibility with polar compounds such as 'sulfonated oils, soaps, fatty alcohol sulfates, etc. Thus it is found that certain highly sulfonated olive and castor oils will form turbid solutions when mixed with mineral oil. If a I ,trile or mixture of such nitriles is used as a third component of the formula, a clear, homogeneous solution results. f v

The nitriles are excellent solvents for soaps and other emulsifying or dispersing agents. Thus, for example, oleic and stearic acid amine soaps when mixed with oleonitrile or the nitriles obtained from lard oil fatty acids form clear, stable solutions which may be applied to textile fibers 'by the usual methods. Alternatively, the solution of soap in the nitrile may be mixed with other oils, fats, or waxes toform conditioning agents of diverse types. g

The 'nitriles not only lend themselves readily to the formation of stable-oils, but also are easily. adaptable to emulsiiication processes. For example, a solution of soap and/or sulfonated oil in oleonitrile or stearonitrile forms a finely dispersed, stable emulsion when mixed with water. Or the nitrile soap solution may be mixed with a mineral oil and/ or a vegetable oil and the whole emulsified by suitable treatment with water.

My invention will be more fully understood by reference to the following examples which are inof illustration and not as a limitation thereof.

Example 1 Continuous filament, 150 denier, celluloseacetate warp yarn is lubricated by the application thereto of lauronitrile. In this case the nitrile is applied as such in an amount corresponding to 4%. based on the weight of the yarn by means over porcelain and'steel lubricants.

example, oleoniyam was appreciably lower than that of an applicator roll or equivalent device. It was found that when the lubricated yarn was passed guides that the friction, as measured by the grams pull developed in the developed in similar yarn lubricated with ordinary textile Example 2 A cellulose acetate yarn similar to that of Example 1 was treated under the same conditions with 5% of stearonitrile. In this case the friction was also appreciably reduced below that developed when treating the same yarn with other textile lubricants.

Example 3 A cellulose acetate yarn of the same type as that referred to in Example 1 was treated by the application thereto of 3% of oleonitrile'. Again the friction was reduced below that obtained by the application to the same yarn of ordinary textile lubricants.

A comparison of the improved results to be obtained in the lubrication of textile yarns by ,means of the nitriles. and'by means of ordinary yarn lubricants can be obtained by reference to the following table which embodies the results of tests run on the same'type of cellulose acetate yarn lubricated with the same amounts of several difierent lubricants under identical conditions. The amount of friction or drag produced as these lubricated yarns were drawn over both porcehigh molecular weight ni- Glycol oleate on standing.

lain and steel guides was measured on a machine adapted for this purpose. The figures used in the table representthe grams of force required to pull the lubricated yarn over the porcelain and steel guides.

I Grams pull developed Lubricating agent Porcelain Steel guides guides Lauronitrile sasaassasss eessssseeegz The yarn employed in running the tests from which the above denier, brightluster cellulose acetate yarn twisted data were obtained was to three turns per inch.

} Example 4 V A cellulose acetate yarn is lubricated by the application of .aclear oil having the following composition:

' V Parts Sulfonated olive oil 30 Mineral oil (55 secs. visc.) 55 Oleonitrile l5 In this formula the is formed by the combination of these various ingredients which will not separate into phases The conditioning fluid may be applied as such by means of a wick, roll or equivalent device or it may be applied as an emulsion.

dispersed in water and i Aclear,

- weight water.

emulsion.

, clear, homogeneous Mineral oil (55 secs. visc.) 60 Triethanolamlne oleate-.-. 27 Lauronitrile i3 Triethanolamine oleate is insoluble in mineral oil, but a clear, homogeneous, stable solution may be prepared by employing'lauronitrile as a blending agent or cosolvent in the proportions shown above. This composition may be applied to fibers; in various stages of processing as an oil or as an aqueous Example 6 may be employed as a stable oil, or as an aqueous the following composition:

A composition which emulsion, may have Parts Coconut oil 60 -8tearonitrile 40 Stoddard solvent 200 may be applied to filaments or fibers of cellulose acetate-mother. cellulose organic acid esters to the extent oi 0.5 to 5.0% based on the weight of the yarn. It imparts to This composition the yarnv an extremely low'coeillcient oi'iriction.

The particular method of app ication-o1 the yarn treating compositions of myinvention to the yarn will depend largely upon the nature of use for which it is intended. In general, the compositions may be applied by any 01' the standard procedures such as roll, wick, bath, or spray application. If the'yam is in continuous filament form, compositions may be applied just as the yarn emerges from the spinning cabinet, or while passing from package to pack- Likewise, the lubricant may be applied during twisting, winding, crepeing or similar operations. In the case of cut staple fibers, the

be conveniently applied in form oi'an emulsion bath or spray,- preferably after any desired special treatment or the yarn such as crimping or the like.

While I have found it staple fibers.

-. outstanding results as aseassc my invention resides in long-chain nitriles give yarn lubricating agents,

.As indicated above, the discovery that the particularly as lubricating and conditioning What I claim and desire'to secure by Letters Patent of the United States is:

,1., The process of conditioning a cellulose organic derivativetextile of or containing cellulose acetate to render it amenable to knitting, weaving, spinning, carding, the like which comprises app ying thereto a composition containing, stearonitrile.

4. The processor conditioning yarn composed knitting, weaving, spinning. carding, the like which comprises applying thereto a composition containing oleonitrile. CALDWELL JOHN R. 

